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Tips for Booking a Vacation Rental in 2021

Jim Reese | 3/8/2021 (updated 6/7/2022)

Bookings for vacation rentals on the Cape & Islands have hit record levels - over 100% increase from recent years. After a long, housebound winter during the pandemic, vacationers are eager to make their summer plans and secure a rental early.

Despite the record demand, however, there are many options still available if you are flexible in your search process. There are still over 300 rentals available for each week this summer, and new listings are being activated every day.

Below are some tips for finding a rental that is right for you!

Relax Your Criteria

By broadening your search in terms of location and/or dates, you will greatly increase your available options.

Flexible Dates

The most popular weeks are in the heart of the summer (weeks starting July 10 through August 7). Searching outside this time frame will provide more results. In some cases, prices are better, too!

In particular, if your schedule permits, look for the bookends of the summer where the availability is higher.

  • June 26 - 30%
  • August 21 – 35%
  • August 28 – 53%

While August 28th is not always an option for families with kids going back to school, June 26th is more feasible given that schools are getting out earlier this year without many snow days.

Of course, you will find even greater availability in the weeks immediately before and after summer.


This year, a narrow search in a particular town is not likely to find many options that meet your criteria. Consider opening up your search to the entire Cape, or all of Martha’s Vineyard or Nantucket.

Book Near a Pond

Rentals on the beach or with a pool are always in demand, but not to be overlooked are the rentals near the many ponds providing ample opportunities for swimming, boating, and fishing. Don’t have a boat? Have kayaks and canoes delivered directly to the rental. And the local beaches are almost always just a short drive away to enjoy a traditional seaside beach day.

Concerned About Cancellations?

First, this year is a lot different from spring of 2020. At this time last year, vacation rentals were banned and did not open up until June 8th. A rental ban will not happen again this year.

However, if you are concerned that a situation may require you to cancel your rental, ask the homeowner about their cancellation policy. Many owners have relaxed their policies due to the pandemic. You could also look into adding travel insurance